Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Large Scale Practical Synthesis of Enantiomerically Pure cis-4-Amino-3-fluoro-1-methylpiperidine via Rhodium-Catalyzed Asymmetric Hydrogenation of a Tetrasubstituted Fluoroalkene.Formula: C14H8BF4Rh.
The development of multi kilo-gram scale green and economical synthetic route of enantiomerically pure cis-4-amino-3-fluoro-1-methylpiperidine I was described. The synthesis featured a highly regio-, chemo- and enantioselective asym. hydrogenation of N-benzyl-4-((tert-butoxycarbonyl)amino)-5-fluoro-tetrahydropyridinium chloride. No purification or chiral enrichment was necessary due to high selectivity resulting from proper selection of catalyst system Rh(NBD)2(BF4) and Walphos 003. The crude product N-benzyl piperidine was carried directly to N-methylpiperidine utilizing a highly effective one-pot debenzylation and reductive amination protocol. The target compound 1•2HCl was prepared in 66-68% overall yield with >99% ee and >98.5% purity from available compound 3-fluoropyridin-4-amine with a Process Mass Intensity of 150.
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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider